NO314803B1 - 2-Amino-6-(2-substituert-4-fenoksy)-substituerte pyridiner, anvendelse derav, farmasöytiske preparater inneholdende disse, og mellomprodukterved fremstilling derav - Google Patents

2-Amino-6-(2-substituert-4-fenoksy)-substituerte pyridiner, anvendelse derav, farmasöytiske preparater inneholdende disse, og mellomprodukterved fremstilling derav Download PDF

Info

Publication number: NO314803B1
Authority: NO; Norway
Prior art keywords: alkyl; ring; nmr; disease; formula
Prior art date: 1997-02-10

Application number

NO19993823A

Other languages

English (en)

Norwegian (no)

Other versions

NO993823L (no

NO993823D0 (no

Inventor

Iii John Adams Lowe

Jolanta Nowakowski

Robert Alfred Volkmann

Original Assignee

Pfizer Prod Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-02-10

Filing date

1999-08-09

Publication date

2003-05-26

1999-08-09 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

1999-08-09 Publication of NO993823L publication Critical patent/NO993823L/no

1999-08-09 Publication of NO993823D0 publication Critical patent/NO993823D0/no

2003-05-26 Publication of NO314803B1 publication Critical patent/NO314803B1/no

Links

238000002360 preparation method Methods 0.000 title claims description 16
239000008194 pharmaceutical composition Substances 0.000 title claims description 8
239000000543 intermediate Substances 0.000 title description 7
150000003222 pyridines Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 184
125000000217 alkyl group Chemical group 0.000 claims description 35
-1 ( C 1 -C 6 alkyl Chemical group 0.000 claims description 28
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 26
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 26
239000001257 hydrogen Substances 0.000 claims description 26
229910052739 hydrogen Inorganic materials 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 24
239000000203 mixture Substances 0.000 claims description 21
229910052757 nitrogen Inorganic materials 0.000 claims description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
102000008299 Nitric Oxide Synthase Human genes 0.000 claims description 18
108010021487 Nitric Oxide Synthase Proteins 0.000 claims description 18
208000002193 Pain Diseases 0.000 claims description 17
206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 16
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 16
208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 16
230000001154 acute effect Effects 0.000 claims description 16
208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 16
201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 16
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
241000124008 Mammalia Species 0.000 claims description 15
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
IOEPOEDBBPRAEI-UHFFFAOYSA-N 1,2-dihydroisoquinoline Chemical group C1=CC=C2CNC=CC2=C1 IOEPOEDBBPRAEI-UHFFFAOYSA-N 0.000 claims description 12
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 12
125000004122 cyclic group Chemical group 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 12
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 11
206010040070 Septic Shock Diseases 0.000 claims description 10
206010013663 drug dependence Diseases 0.000 claims description 10
150000002431 hydrogen Chemical class 0.000 claims description 10
229920006395 saturated elastomer Polymers 0.000 claims description 10
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206010028980 Neoplasm Diseases 0.000 claims description 9
201000011510 cancer Diseases 0.000 claims description 9
208000027866 inflammatory disease Diseases 0.000 claims description 9
230000002265 prevention Effects 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
230000036303 septic shock Effects 0.000 claims description 9
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
208000030507 AIDS Diseases 0.000 claims description 8
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206010047700 Vomiting Diseases 0.000 claims description 8
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230000036506 anxiety Effects 0.000 claims description 8
125000003710 aryl alkyl group Chemical group 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
208000033679 diabetic kidney disease Diseases 0.000 claims description 8
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230000002401 inhibitory effect Effects 0.000 claims description 8
208000002780 macular degeneration Diseases 0.000 claims description 8
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201000006417 multiple sclerosis Diseases 0.000 claims description 8
230000004770 neurodegeneration Effects 0.000 claims description 8
208000015122 neurodegenerative disease Diseases 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
201000008482 osteoarthritis Diseases 0.000 claims description 8
230000016087 ovulation Effects 0.000 claims description 8
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
206010039073 rheumatoid arthritis Diseases 0.000 claims description 8
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201000009032 substance abuse Diseases 0.000 claims description 8
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239000003937 drug carrier Substances 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
230000001225 therapeutic effect Effects 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
125000004429 atom Chemical group 0.000 claims description 5
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 4
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
206010029350 Neurotoxicity Diseases 0.000 claims description 4
206010044221 Toxic encephalopathy Diseases 0.000 claims description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
210000002569 neuron Anatomy 0.000 claims description 4
230000007135 neurotoxicity Effects 0.000 claims description 4
231100000228 neurotoxicity Toxicity 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 4
230000001988 toxicity Effects 0.000 claims description 4
231100000419 toxicity Toxicity 0.000 claims description 4
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 2
125000000168 pyrrolyl group Chemical group 0.000 claims 2
125000001589 carboacyl group Chemical group 0.000 claims 1
238000005481 NMR spectroscopy Methods 0.000 description 150
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 143
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 62
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 57
238000006243 chemical reaction Methods 0.000 description 54
235000019439 ethyl acetate Nutrition 0.000 description 47
238000010992 reflux Methods 0.000 description 45
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 44
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
239000011541 reaction mixture Substances 0.000 description 38
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 35
239000007787 solid Substances 0.000 description 35
239000000243 solution Substances 0.000 description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 31
238000000034 method Methods 0.000 description 30
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 26
239000012043 crude product Substances 0.000 description 24
239000012299 nitrogen atmosphere Substances 0.000 description 23
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
239000012267 brine Substances 0.000 description 22
229910052938 sodium sulfate Inorganic materials 0.000 description 22
235000011152 sodium sulphate Nutrition 0.000 description 22
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 21
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 19
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
239000002904 solvent Substances 0.000 description 17
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HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical class OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
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QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 13
238000004458 analytical method Methods 0.000 description 13
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OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 11
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 11
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238000003756 stirring Methods 0.000 description 11
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208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
229910000027 potassium carbonate Inorganic materials 0.000 description 10
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102100022397 Nitric oxide synthase, brain Human genes 0.000 description 8
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AEKQCMMJOMDJPC-UHFFFAOYSA-N 2-bromo-6-(2,5-dimethylpyrrol-1-yl)pyridine Chemical compound CC1=CC=C(C)N1C1=CC=CC(Br)=N1 AEKQCMMJOMDJPC-UHFFFAOYSA-N 0.000 description 6
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A61P25/06—Antimigraine agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/08—Plasma substitutes; Perfusion solutions; Dialytics or haemodialytics; Drugs for electrolytic or acid-base disorders, e.g. hypovolemic shock
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Ophthalmology & Optometry (AREA)
Rheumatology (AREA)
Diabetes (AREA)
Addiction (AREA)
Hospice & Palliative Care (AREA)
Hematology (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Hydrogenated Pyridines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO19993823A 1997-02-10 1999-08-09 2-Amino-6-(2-substituert-4-fenoksy)-substituerte pyridiner, anvendelse derav, farmasöytiske preparater inneholdende disse, og mellomprodukterved fremstilling derav NO314803B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US3753397P	1997-02-10	1997-02-10
PCT/IB1998/000112 WO1998034919A1 (en)	1997-02-10	1998-01-29	2-amino-6-(2-substituted-4-phenoxy)-substituted-pyridines

Publications (3)

Publication Number	Publication Date
NO993823L NO993823L (no)	1999-08-09
NO993823D0 NO993823D0 (no)	1999-08-09
NO314803B1 true NO314803B1 (no)	2003-05-26

Family

ID=21894849

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19993823A NO314803B1 (no)	1997-02-10	1999-08-09	2-Amino-6-(2-substituert-4-fenoksy)-substituerte pyridiner, anvendelse derav, farmasöytiske preparater inneholdende disse, og mellomprodukterved fremstilling derav

Country Status (44)

Country	Link
US (2)	US20010007873A1 (is)
EP (1)	EP0958282B1 (is)
JP (1)	JP3505189B2 (is)
KR (1)	KR100460399B1 (is)
CN (3)	CN1523015A (is)
AP (1)	AP833A (is)
AR (1)	AR011117A1 (is)
AT (1)	ATE271544T1 (is)
AU (1)	AU744313B2 (is)
BG (1)	BG103633A (is)
BR (1)	BR9811093A (is)
CA (1)	CA2277990C (is)
CO (1)	CO4920225A1 (is)
CZ (1)	CZ292135B6 (is)
DE (1)	DE69825147T2 (is)
DK (1)	DK0958282T3 (is)
DZ (1)	DZ2414A1 (is)
EA (1)	EA003834B1 (is)
ES (1)	ES2224354T3 (is)
GT (1)	GT199800032A (is)
HN (1)	HN1998000030A (is)
HR (1)	HRP980069A2 (is)
HU (1)	HUP0000762A3 (is)
IL (1)	IL130898A0 (is)
IS (1)	IS5118A (is)
MA (1)	MA27676A1 (is)
MY (1)	MY120976A (is)
NO (1)	NO314803B1 (is)
NZ (2)	NZ518345A (is)
OA (1)	OA11084A (is)
PA (1)	PA8446301A1 (is)
PE (1)	PE58599A1 (is)
PL (1)	PL335161A1 (is)
PT (1)	PT958282E (is)
SI (1)	SI0958282T1 (is)
SK (1)	SK101199A3 (is)
TN (1)	TNSN98024A1 (is)
TR (1)	TR199901917T2 (is)
TW (1)	TW458969B (is)
UA (1)	UA64740C2 (is)
UY (1)	UY24881A1 (is)
WO (1)	WO1998034919A1 (is)
YU (1)	YU35699A (is)
ZA (1)	ZA981017B (is)

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HUP0102236A3 (en) *	1998-06-03	2003-01-28	Pfizer Prod Inc	2-aminopyridines containing fused ring substituents as nitric oxide synthase inhibitors and pharmaceutical compositions containing them and their use
OA11595A (en) *	1998-08-11	2004-08-19	Pfizer Prod Inc	New pharmaceutical uses for NOS inhibitors.
US7115557B2 (en)	1998-09-25	2006-10-03	Sciaticon Ab	Use of certain drugs for treating nerve root injury
SE9803710L (sv)	1998-09-25	2000-03-26	A & Science Invest Ab	Användning av vissa substanser för behandling av nervrotsskador
NZ512912A (en) *	1999-02-25	2003-07-25	Pfizer Prod Inc	2-aminopyridine derivatives having a fused ring substituent are useful for inhibiting the activity of a nitric oxide synthase
FR2812635B1 (fr) *	2000-08-01	2002-10-11	Aventis Pharma Sa	Nouveaux composes heterocycliques, preparation et utilisation comme medicaments notamment comme anti- bacteriens
GB0019006D0 (en) *	2000-08-04	2000-09-20	Astrazeneca Ab	Novel compounds
US20030232739A1 (en) *	2001-08-15	2003-12-18	Pfizer Inc.	Pharmaceutical combinations comprising a NOS inhibitor and an NMDA receptor antagonist
US20030045449A1 (en) *	2001-08-15	2003-03-06	Pfizer, Inc.	Pharmaceutical combinations for the treatment of neurodegenerative diseases
US6803470B2 (en)	2001-10-10	2004-10-12	Pfizer Inc	2-amino-6-(2,4,5-substituted-phenyl)-pyridines
DOP2002000467A (es) *	2001-10-10	2003-04-15	Pfizer Prod Inc	2-amino-6 (fenilo sustituido en las posiciones 2,4,5)-piridinas
US7045652B2 (en)	2002-07-03	2006-05-16	Pfizer Inc	Processes for preparing substituted aryl boronic acids
US20040092741A1 (en) *	2002-11-08	2004-05-13	Pfizer Inc	Substituted pyridines via boronic acid coupling
WO2005007627A1 (ja) *	2003-07-18	2005-01-27	Nihon Nohyaku Co., Ltd.	フェニルピリジン誘導体、その中間体及びこれを有効成分とする除草剤
JP2008545616A (ja) *	2005-02-21	2008-12-18	プロキシマジェンエルティーディー	ジスキネジーの阻害または治療
GB0607196D0 (en) *	2006-04-11	2006-05-17	Prosidion Ltd	G-protein coupled receptor agonists
WO2008080938A1 (en) *	2006-12-28	2008-07-10	Basf Se	Use 2-substituted pyridines for cancer treatment
UA105182C2 (ru)	2008-07-03	2014-04-25	Ньюрексон, Інк.	Бензоксазины, бензотиазины и родственные соединения, которые имеют ингибирующую nos активность
CN108017603B (zh)	2013-02-28	2021-07-23	株式会社蒂奥姆生物	三环化合物及其用途
US10689344B2 (en) *	2013-11-07	2020-06-23	University Of Kansas	Biphenylamide derivative Hsp90 inhibitors
US10562858B2 (en) *	2014-08-13	2020-02-18	Meiji Seika Pharma Co., Ltd.	Crystalline anti-trichophyton agents and preparation process thereof
CN106265640B (zh) *	2016-08-11	2019-05-14	吉林大学	Appa在制备治疗糖尿病肾病药物中的应用
CN108069831B (zh) *	2018-01-25	2020-11-24	上海恩氟佳科技有限公司	一种合成2,3-二甲基-4-氟苯酚的方法

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WO1994014780A1 (en) *	1992-12-18	1994-07-07	The Wellcome Foundation Limited	Pyrimidine, pyridine, pteridinone and indazole derivatives as enzyme inhibitors
ATE177078T1 (de) *	1993-10-21	1999-03-15	Searle & Co	Amidino-derivate als no-synthetase inhibitoren
WO1996018616A1 (en) *	1994-12-12	1996-06-20	Merck & Co., Inc.	Substituted 2-aminopyridines as inhibitors of nitric oxide synthase
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1998
- 1998-01-29 BR BR9811093-4A patent/BR9811093A/pt not_active Application Discontinuation
- 1998-01-29 WO PCT/IB1998/000112 patent/WO1998034919A1/en not_active Ceased
- 1998-01-29 CN CNA2004100073282A patent/CN1523015A/zh active Pending
- 1998-01-29 IL IL13089898A patent/IL130898A0/xx unknown
- 1998-01-29 AT AT98900635T patent/ATE271544T1/de not_active IP Right Cessation
- 1998-01-29 PL PL98335161A patent/PL335161A1/xx unknown
- 1998-01-29 DK DK98900635T patent/DK0958282T3/da active
- 1998-01-29 DE DE69825147T patent/DE69825147T2/de not_active Expired - Fee Related
- 1998-01-29 YU YU35699A patent/YU35699A/sh unknown
- 1998-01-29 SK SK1011-99A patent/SK101199A3/sk unknown
- 1998-01-29 KR KR10-1999-7007065A patent/KR100460399B1/ko not_active Expired - Fee Related
- 1998-01-29 CN CN98802392A patent/CN1246848A/zh active Pending
- 1998-01-29 SI SI9830699T patent/SI0958282T1/xx unknown
- 1998-01-29 NZ NZ518345A patent/NZ518345A/en unknown
- 1998-01-29 AU AU55727/98A patent/AU744313B2/en not_active Ceased
- 1998-01-29 TR TR1999/01917T patent/TR199901917T2/xx unknown
- 1998-01-29 UA UA99084543A patent/UA64740C2/uk unknown
- 1998-01-29 CZ CZ19992769A patent/CZ292135B6/cs not_active IP Right Cessation
- 1998-01-29 ES ES98900635T patent/ES2224354T3/es not_active Expired - Lifetime
- 1998-01-29 CA CA002277990A patent/CA2277990C/en not_active Expired - Fee Related
- 1998-01-29 NZ NZ336623A patent/NZ336623A/xx unknown
- 1998-01-29 EA EA199900632A patent/EA003834B1/ru not_active IP Right Cessation
- 1998-01-29 HU HU0000762A patent/HUP0000762A3/hu unknown
- 1998-01-29 PT PT98900635T patent/PT958282E/pt unknown
- 1998-01-29 CN CNA031086047A patent/CN1515554A/zh active Pending
- 1998-01-29 EP EP98900635A patent/EP0958282B1/en not_active Expired - Lifetime
- 1998-01-29 JP JP53404898A patent/JP3505189B2/ja not_active Expired - Fee Related
- 1998-02-03 TW TW087101311A patent/TW458969B/zh not_active IP Right Cessation
- 1998-02-05 PE PE1998000082A patent/PE58599A1/es not_active Application Discontinuation
- 1998-02-05 AP APAP/P/1998/001178A patent/AP833A/en active
- 1998-02-06 MY MYPI98000488A patent/MY120976A/en unknown
- 1998-02-06 UY UY24881A patent/UY24881A1/es not_active Application Discontinuation
- 1998-02-09 DZ DZ980024A patent/DZ2414A1/xx active
- 1998-02-09 HN HN1998000030A patent/HN1998000030A/es unknown
- 1998-02-09 MA MA24958A patent/MA27676A1/fr unknown
- 1998-02-09 ZA ZA9801017A patent/ZA981017B/xx unknown
- 1998-02-09 AR ARP980100551A patent/AR011117A1/es not_active Application Discontinuation
- 1998-02-09 TN TNTNSN98024A patent/TNSN98024A1/fr unknown
- 1998-02-10 PA PA19988446301A patent/PA8446301A1/es unknown
- 1998-02-10 CO CO98006875A patent/CO4920225A1/es unknown
- 1998-02-10 HR HR60/037,533A patent/HRP980069A2/hr not_active Application Discontinuation
- 1998-02-11 GT GT199800032A patent/GT199800032A/es unknown
- 1998-07-31 US US09/127,158 patent/US20010007873A1/en not_active Abandoned
1999
- 1999-07-16 IS IS5118A patent/IS5118A/is unknown
- 1999-08-03 BG BG103633A patent/BG103633A/bg unknown
- 1999-08-06 OA OA9900173A patent/OA11084A/en unknown
- 1999-08-09 NO NO19993823A patent/NO314803B1/no unknown
2003
- 2003-02-20 US US10/371,357 patent/US20030162765A1/en not_active Abandoned

Also Published As

Publication number	Publication date
TNSN98024A1 (fr)	2005-03-15
CN1515554A (zh)	2004-07-28
DZ2414A1 (fr)	2003-01-04
DK0958282T3 (da)	2004-11-29
AU744313B2 (en)	2002-02-21
TW458969B (en)	2001-10-11
GT199800032A (es)	1998-02-11
CA2277990C (en)	2006-08-01
NO993823L (no)	1999-08-09
EA003834B1 (ru)	2003-10-30
AU5572798A (en)	1998-08-26
PL335161A1 (en)	2000-04-10
EP0958282A1 (en)	1999-11-24
CZ276999A3 (cs)	2000-05-17
ZA981017B (en)	1999-08-10
PE58599A1 (es)	1999-06-12
CN1246848A (zh)	2000-03-08
US20030162765A1 (en)	2003-08-28
AP833A (en)	2000-05-10
CA2277990A1 (en)	1998-08-13
DE69825147D1 (de)	2004-08-26
KR100460399B1 (ko)	2004-12-08
CO4920225A1 (es)	2000-05-29
IL130898A0 (en)	2001-01-28
YU35699A (sh)	2002-06-19
MY120976A (en)	2005-12-30
IS5118A (is)	1999-07-29
HRP980069A2 (en)	1998-12-31
UA64740C2 (uk)	2004-03-15
ES2224354T3 (es)	2005-03-01
HUP0000762A3 (en)	2000-10-30
EA199900632A1 (ru)	2000-02-28
JP2000509408A (ja)	2000-07-25
SK101199A3 (en)	2000-10-09
AR011117A1 (es)	2000-08-02
HN1998000030A (es)	1998-10-22
BG103633A (bg)	2000-11-30
EP0958282B1 (en)	2004-07-21
CN1523015A (zh)	2004-08-25
HUP0000762A2 (hu)	2000-09-28
MA27676A1 (fr)	2006-01-02
SI0958282T1 (en)	2005-02-28
NZ336623A (en)	2000-11-24
DE69825147T2 (de)	2005-08-04
JP3505189B2 (ja)	2004-03-08
NO993823D0 (no)	1999-08-09
TR199901917T2 (xx)	1999-12-21
US20010007873A1 (en)	2001-07-12
ATE271544T1 (de)	2004-08-15
PT958282E (pt)	2004-11-30
OA11084A (en)	2002-03-15
PA8446301A1 (es)	2000-05-24
UY24881A1 (es)	2000-12-29
WO1998034919A1 (en)	1998-08-13
BR9811093A (pt)	2000-07-18
NZ518345A (en)	2005-02-25
KR20000070803A (ko)	2000-11-25
CZ292135B6 (cs)	2003-08-13

Publication	Publication Date	Title
NO314803B1 (no)	2003-05-26	2-Amino-6-(2-substituert-4-fenoksy)-substituerte pyridiner, anvendelse derav, farmasöytiske preparater inneholdende disse, og mellomprodukterved fremstilling derav
AU2012255690B2 (en)	2015-06-11	Amine derivatives as potassium channel blockers
IL154079A (en)	2008-03-20	History of 4-phenyl-pyridine used as neurokinin-1 receptor antagonists
SK70899A3 (en)	2002-04-04	6-phenylpyridyl-2-amine derivatives useful as nos inhibitors
CS203970B2 (en)	1981-03-31	Method of producing novel heterocyclyl-oxy-hydroxy-amino-propanes
KR20190013555A (ko)	2019-02-11	프로테인 카이네이즈에 대한 선택적 억제제의 합성에 유용한 중간체 및 이의 제조방법
CA3085879A1 (en)	2019-06-27	Substituted pyrrolidine amides ii
NO327882B1 (no)	2009-10-12	Terapeutisk aktive cyklopropanforbindelser, fremsgangsmater for fremstilling derav, farmasoytiske sammensetninger inneholdende disse samt anvendelse derav for fremstilling av farmasoytiske sammensetninger.
AU661198B2 (en)	1995-07-13	1-heteroarylazetidines and -pyrrolidines, process for their preparation and pharmaceutical compositions containing them
AU769233B2 (en)	2004-01-22	2-amino-6-(2-substituted-4-phenoxy)-substituted-pyridines
CN107074780A (zh)	2017-08-18	用于生产嘧啶‑1‑醇化合物及其中间体的方法
AU727647B2 (en)	2000-12-21	Method of production and method of separation of 2,4'-dipyridyl derivatives and methods of production of benzoxazepine derivatives and salts thereof
MXPA99007398A (en)	2000-07-01	2-amino-6-(2-substituted-4-phenoxy)-substituted-pyridines
EP1434624B1 (en)	2006-11-02	2-amino-6-(2,4,5-substituted-phenyl)-pyridines for use as nitric oxide synthase inhibitors
AU2002341234A1 (en)	2003-04-22	2-amino-6-(2,4,5-substituted-phenyl)-pyridines for use as nitric oxide synthase inhibitors
HK40027082A (en)	2021-01-15	Novel intermediates useful for the synthesis of aminopyrimidine derivatives, process for preparing the same, and process for preparing aminopyrimidine derivatives using the same
MXPA00002028A (en)	2001-05-17	Branched alkoxy-subsituted 2-aminopyridines as nos inhibitors